Water → N-(6,7-dihydro-5H-dibenzo[a,c]cyclohepten-4-yl)methyl cis-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxamide

HRID 2412569Notes

Reaction equation

HRID 2412569 reaction equation
[CH:1]1[C:6]2[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH2:9][CH2:10][CH2:11][C:5]=2[C:4]([CH2:16][NH2:17])=[CH:3][CH:2]=1.[Cl:18][C:19]([C:29]([F:32])([F:31])[F:30])=[CH:20][C@@H:21]1[C@H:23]([C:24](Cl)=[O:25])[C:22]1([CH3:28])[CH3:27].N1C=CC=CC=1.O>C1C=CC=CC=1>[CH:1]1[C:6]2[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH2:9][CH2:10][CH2:11][C:5]=2[C:4]([CH2:16][NH:17][C:24]([C@H:23]2[C@@H:21]([CH:20]=[C:19]([Cl:18])[C:29]([F:32])([F:30])[F:31])[C:22]2([CH3:28])[CH3:27])=[O:25])=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 133912796,7-dihydro-5H-dibenzo[a,c]cyclohepten-4-methanamineHCID 86737382cis-3-(2-Chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarbonyl chloride

Product 1

HCID 86739869N-(6,7-dihydro-5H-dibenzo[a,c]cyclohepten-4-yl)methyl cis-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxamideYield 86.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution containing 6,7-dihydro-5H-dibenzo[a,c]cyclohepten-4-methanamine (0.5 gram, 0.0022 mole) and benzene (40 ml) was added dropwise to a stirred solution of cis-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid chloride (0.75 gram, 0.0029 mole) and pyridine (1.0 gram, 0.013 mole) in benzene (20 ml). The resulting mixture was stirred at room temperature for approximately 16 hours, poured into water and the total extracted with three 100 ml portions of diethyl ether. The combined extracts were washed with a 10% aqueous sodium carbonate solution (100 ml) followed by two 50 ml portions of water. The washed extracts were dried over anhydrous magnesium sulfate, and filtered. The solvent was evaporated from the filtrate under reduced pressure leaving a yellow residue. This residue was purified by column chromatography on silica gel, elution with benzene:diethyl ether (3:1), to yield N-(6,7-dihydro-5H-dibenzo[a,c]cyclohepten-4-yl)methyl cis-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxamide as a colorless solid (0.85 gram, mp 65°-70°).

Workup

  1. extractionthe total extracted with three 100 ml portions of diethyl ether
  2. washThe combined extracts were washed with a 10% aqueous sodium carbonate solution (100 ml)
  3. dry with materialThe washed extracts were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated from the filtrate under reduced pressure
  6. customleaving a yellow residue
  7. customThis residue was purified by column chromatography on silica gel, elution with benzene:diethyl ether (3:1)

Sources & evidence

ORD record
ord-abc598274394438286072deac223e4e4
Source dataset
uspto-grants-1985_01
Patent number
US04493844

Reaction notes

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